Vacation Rental Specialist

Extenteam is the AI-driven operations platform for short-term rental property management, headquartered in Miami and founded in 2021. Our platform, Shared Services, handles guest communication and daily operational workflows for 80,000+ properties by pairing an AI orchestration layer with a shared-services team of hospitality-trained specialists, so no guest inquiry goes unanswered, day or night, and no property manager has to staff for the 2am cancellation themselves.

We're industry-only: every workflow, integration, and agent we hire is built around property management specifically, not bolted on from a generalist platform. As we push more of that platform toward AI-led automation and self-serve tools, the software our own Shared Services team works in every day has to keep pace, that's this role.

Our company embraces a management style inspired by the ideals of "founder mode," as championed by Airbnb’s Brian Chesky. This means a hands-on, visionary approach to leadership, with a relentless focus on innovation, product excellence, and customer-centric decision-making. We encourage proactive problem-solving, direct involvement in key initiatives, and a collaborative, high-performance culture.

To learn more about the "founder mode" philosophy and how it shapes our operations, you can explore this link. Understanding this mindset will provide valuable context for how we operate and what we value in our team members.

You'll be the day-to-day engine of both businesses: guest communication, turnover and vendor coordination, plumbing scheduling and dispatch, social media, and preparing the books for owner approval. Plumbing slows down in winter, so the workload shifts toward the rental business in those months, but the core responsibilities stay the same year-round.

We're looking for an organized, detail-oriented person who works well independently, follows documented procedures, communicates warmly in writing and by phone, and enjoys juggling many moving parts.

We're not a typical corporation. Our owners are all family, and you'll be in daily, frequent contact with them by message, phone, and video. We work closely, check in often, and look out for one another. The right person won't feel like an employee in a department. They'll feel like part of the family business.

You'll represent our family and our name to guests, customers, and vendors every day, so character matters as much as skills. We're looking for someone who:

• Is honest and trustworthy with guest access codes, customer information, and financial records.
• Thrives with a variable, changing workload: stays flexible, solves problems as they come, and takes initiative without waiting to be asked.
• Owns mistakes and speaks up early, so problems get fixed quickly.
• Communicates openly and often, and welcomes frequent check-ins with the owners.
• Treats guests, customers, cleaners, and vendors with kindness and respect, even in stressful moments.
• Is dependable: works the agreed schedule, follows through, and gives a heads-up when something will be late.
• Is discreet with private matters, both our guests' (many are in town for medical care) and our family's.
• Brings a positive, team-first attitude and takes pride in doing things well.

• Serve as the primary contact for guests booking through Airbnb, Vrbo, and our direct booking site, managing all messaging in our PMS (Hospitable).
• Respond to guest messages, texts, and calls about check-in, smart lock access, Wi-Fi, directions, and house questions.
• Handle the full reservation process: inquiries, bookings, changes, and cancellations.
• Follow up on inquiries and voicemails to turn leads into bookings.
• Respond to complaints with empathy and professionalism, resolving what you can and escalating when needed.
• Monitor and respond to guest reviews, and flag recurring feedback that points to an improvement.
• Update and maintain listings and house manuals (photos, descriptions, amenities, house rules) across all channels.

• Coordinate cleaners and turnovers: weekly schedules, same-day turnovers, early starts on vacant homes, and supply restocking.
• Enter work orders for maintenance issues reported by guests or cleaners.
• Schedule and coordinate maintenance vendors (snow removal, lawn care, repairs) and follow up to confirm work is complete.

• Answer and make calls with residential and commercial plumbing customers.
• Schedule appointments and dispatch jobs to the plumbing team.
• Keep customers informed about arrival times, follow-ups, and next steps.

All financial documents are prepared for the owner's final review and approval.

• Monitor accounts daily and categorize transactions in QuickBooks Online.
• Prepare monthly owner statements and financial reports in Hospitable.
• Prepare invoices for completed plumbing jobs.

• Create, schedule, and post social media content for both businesses.

• Follow our documented SOPs, and help keep them current as processes change.
• Use AI tools and automation to work efficiently and accurately.

• Hands-on experience with Hospitable.
• Vacation rental experience with Airbnb and Vrbo.
• Social media marketing experience (for example, Canva or Meta Business Suite).
• Experience using AI tools such as Claude.ai in day-to-day work.
• Scheduling and dispatch experience in home services or the trades.
• Comfort with business phone and texting platforms and smart lock systems.
• Interest in growing with a family business as it expands.

• Internet speed minimum 30mbps: Needs to be Wired (Buy a dongle if no LAN port)
• i5 11th Gen or higher
• Windows 11 / MacOS Catalina or higher
• Minimum of 8 GB RAM
• Private and quiet dedicated home office area (no roosters, dogs, children's noises in the background)
• Back-ups in case of power or internet provider interruptions
• Good headset and webcam (preferably noise-canceling headset)

• Excellent written and spoken English across phone, text, and email.
• Experience in guest services, reservations, scheduling, or a related field.
• Consistent availability Wednesday–Sunday, 12:00–8:00 PM Central Time.
• Reliable high-speed internet and a quiet workspace suitable for phone calls.
• Strong organization, multitasking, and attention to detail.
• Ability to work independently in a remote environment and follow written procedures.
• Empathy, patience, and a customer-first mindset.
• Critical thinking and problem-solving skills, plus the willingness to ask questions when something is unclear.
• Ability to learn new software quickly.

• Competitive Salary — We offer a competitive salary that reflects the candidate’s experience, skills, and responsibilities.
• Remote Work — This role is 100% remote, allowing flexibility and eliminating daily commute.
• Paid Time Off — Standard leave entitlements (vacation, sick leave, vacation leave) for rest and well-being.
• HMO Coverage — Company-provided HMO plan, offering access to medical services via accredited hospitals and clinics under a Health Maintenance Organization. This helps ensure employees have access to routine checkups, consultations, and coverage for medical care.